The Problem:
Our very likable but absent minded bookkeeper keeps neglecting to pay our IT vendors on time. Just this past week our internet service was disconnected.
Same could happen to many other mission critical accounts (domain registrar, backup MX, anti-virus license, HackerSafe (McAfee secure) service and even an 800 number to name a few).

As the sysadmin, i monitor my severs to make sure they are plugged into the power-outlet.
I believe i should also monitor my services to make sure they are plugged in to their money-outlet.

To compound the problem, when the power goes out someone else will likely notice and notify me. But if a bill is not payed, no one will ever notice until service is lost.
Lost as in losing our domain name which would cause a lot more damage then the power failing on our server.

Possible solutions:
Retrain the bookkeeper = Wishful thinking.
Notify my manager = Already have (via email). Protects me, does not solve problem.
Fire bookkeeper = What makes you so sure the next one will never forget?

Bottom line:
Humans are humans and sooner or later something critical will be royally messed up.
I need a top down, centrally managed system that is capable of sending out alerts - Just like the one that monitors my DC, exchange server etc. - whenever a critical payment is past due. I don't mind if i have to manually enter the payments (until IT vendors start providing APIs for this).

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5 Answers
5

How big is your company? On the one hand, if you're big enough to have an accounting department, they're supposed to be professional and to make payments that are properly dealt with (Purchase Order, etc.) On the other hand, if you're small, you should keep an eye on your own "accounting" to be sure that important payments aren't missed.

At our med-small company (~120 people), we have to rely on the accounting department to pay for some things, but as long as you follow procedures and let them know about deadlines, they do their part. One thing that seems to be different for me than for you is that all IT-related bills come to me for approval as soon as they come in. So I see the phone bill, the cell phone bills, Internet connection invoice, etc., and if there's a problem (e.g. previous payment not made, invoice showed up late and there's not enough time for accounting to cut a cheque), I know about it and can facilitate payment.

Also, in this day of online payment, I often end up paying for things with my own credit card and getting reimbursed, and a pretty big percentage of those are for critical items: name registry, last-minute software orders, etc.

Sorry, the short version is: you don't need a technical solution, you need a management solution, and it should probably start with all the IT bills getting routed to you to check first.

If the bookkeeper can't do their job, I don't see how you can fix it from his/her end. If they can't pay a goddam monthly bill that they have in their possession, how is software going to fix the problem?

I'm astonished that these are manual processes where you work. I've never known anyone to do it that way before. The solution is to do arrange for regular payments to be made by some kind of direct debit. Your bookkeeper is then responsible for ensuring the correct payments are debited at the appropriate times, not paying them. It's a business after all, not a hobby, so don't use hobby methodologies.

If you can reach the URL for checking the expiration dates, you can usually script something to check them. For Zenoss we've the Domain/SSL Certificate Expiration Monitor (http://community.zenoss.org/docs/DOC-4551) and I've seen people script checks for warranty expiration for Dell, IBM and Apple hardware. Might be a good starter to look at how you'd integrate it with your usual network monitoring.